United States Patent Office Patented July 1, 1969

Total Page:16

File Type:pdf, Size:1020Kb

United States Patent Office Patented July 1, 1969 3,453,337 United States Patent Office Patented July 1, 1969 1. 2 3,453,337 FLUORINATION OF HALOGENATED The presence in the reaction mixture of the two fluo ORGANIC COMPOUNDS rides, or the complex fluoride enables better yields of Royston Henry Bennett and David Walter Cottrell, Ayon highly fluorinated products to be obtained under less mouth, England, assignors to Imperial Smelting Cor severe reaction condions, markedly increases the amount poration (N.S.C.) Limited, London, England, a British of fluorination reagent reacted under otherwise similar company conditions and enables the fluorination reaction to be No brawing. Filed Feb. 19, 1965, Ser. No. 434,128 carried out (for the same yield of product) at a lower Claims priority, application Great Britain, Feb. 26, 1964, temperature with the consequent use of less costly ma 7,932/64 terials and techniques of reactor construction. The pres Int, C. C07c 25/04 10 ence of the fluorides enables the vapor phase reaction U.S. C. 260-650 2 Claims to be carried out (for the same yields) at lower pressure This invention relates to the fluorination of organic than the pressure involved in the reactions using only halogen compounds and more especially to a process the alkali metal fluorides as proposed hitherto. The fur for the production of highly fluorinated aromatic com ther possibility of using a continuous flow apparatus such pounds by the replacement of higher halogen atoms in 15 as a fluidised reactor will be apparent to those familiar halogeno-aromatic compounds by fluorine atoms. with the art. The presence of the two fluorides or com Aromatic halogenocarbons containing carbon and halo plex fluoride enables a lower temperature to be em gen atoms only can be reacted with alkali fluorides ployed than was hitherto believed to be necessary, with under various conditions to give yields of halofluoro a consequent reduction in the extent of thermal degrada aromatic compounds. However, where high yields of 20 tion. Low thermal degradation is a considerable advantage highly fluorinated aromatic compounds are required, this in that the reduction in the amount of tar-like degrada process suffers from disadvantages in that drastic reaction tion product facilitates the regeneration of the inorganic conditions and expensive fluorinating reagents are neces residues containing metal chloride plus unreacted metal sary. For example, in the reaction of hexachlorobenzene fluoride, into metal fluoride. This regeneration of the with alkali metal fluorides to give hexafluorobenzene, the 25 alkali metal fluoride is readily achieved by the use of better yields of hexafluorobenzene are only obtainable by hydrogen fluoride as a source of fluorine. Thus, the proc the use of the more expensive inorganic fluorides, e.g. ess including the regeneration is a further feature of caesium fluoride or by high temperature conditions cou the invention. pled with long reaction times using potassium fluoride. It will be a convenient aid to understanding this in The rates of the reactions concerned appear to limit the 30 vention if previous work of the same applicant is con yields of highly fluorinated aromatic compounds ob sidered. tainable under milder conditions and for shorter reaction This earlier work consisted of a process for the pro times. duction of aromatic perhalogenocarbons containing fluo We have now discovered that if the fluorinating agent rine atoms attached to the aromatic nucleus in which is modified by the inclusion of a fluoride chosen from 35 an aromatic compound containing carbon and halogen the group comprising fluorides of elements having a atoms only including at least one halogen atom other valency of between 2 and 6 inclusive, such fluorides being than fluorine is heated with at least one dry monovalent derived from the stable valency states of the elements metal fluoride in the absence of solvents and at a tem concerned, then enhanced yields of highly fluorinated aro perature between 300 and 750° C. matic compounds can be achieved using much milder 40 The metal fluoride used was preferably pelleted, or reaction conditions and shorter reaction times. used in the form of a powder. The reactions could be The invention consists in a process for fluorination of carried out at Sub-atmospheric, atmospheric or super organic halogen compounds in which (a) a mono-valent atmospheric pressures but pressures in the range of 10 to ionic fluoride, such as an alkali metal fluoride, together 50 atmospheres are preferred. Flow systems might be with (b) one or more fluorides of elements having a 45 used but sealed pressure vessels, e.g. autoclaves, were the valency from 2 to 6, present in their stable valency states preferred apparatuses for carrying out this process. are contacted with the organic halogen compounds pref Within the broad scope of that invention there were erably in a vapour phase reaction. preferred conditions for certain types of starting material. The invention further consists in a process for the In one particularly valuable form of the earlier pro production of highly fluorinated aromatic compounds 50 posals the aromatic compound used was a perhalocom in which an aromatic compound containing carbon and pound of formula CsClsF6 where n is an integer from halogen atoms only is contacted with a mixture of in 1 to 6 inclusive. In this case the metal fluoride is pref organic fluorides comprising (a) a monovalent ionic erably caesium, rubidium or potassium fluoride or their fluoride and (b) one or more fluorides of elements hav mixtures, and the temperature may lie between 350° C. ing a valency from 2 to 6, present in their stable valency 55 states (so that the said fluorides have no oxidising prop and 650° C. However, other sub-groups of fluorides and erties when used in accordance with the invention). preferred temperature ranges were shown to be valuable. The monovalent ionic fluoride may be an alkali metal (a) in which in was an integer from 3 to 6 inclusive; the fluoride such as LiF, NaF, RbF, CSF, etc. The other metal fluoride used was potassium fluoride; and the fluoride may conveniently be added to the reaction mix 60 temperature was between 400° C. and 600 C. ture in the form of the alkali metal salts of the corre (b) in which in was 1 or 2; the metal fluoride was potas sponding fluoro-anions. Thus, for example, BFs may be sium fluoride; and the temperature was between 400 added as KBF SnF, may be added as KSnF6. Other -C. and 600° C. complex salts which may be used according to the in (c) in which the metal fluoride used was potassium fluo vention are NaBFA, KPF6, KTiF6 or KSiF6. 65 ride; the temperature was between 500 C. and 600 3,453,337 3 4 C.; and the pressure was between 20 and 50 atmos- Examples 1 to 4 pheres. 8.0 g. hexachlorobenzene were heated for 10 hours at (d) in which in was between 2 and 6 and the metal fluo ride used was sodium fluoride. 500 C. with (1) potassium fluoride, (2) potassium fluo (e) in which in was between 2 and 6; the metal fluoride borate, (3) and (4), a mixture of potassium fluoride with used was sodium fluoride; and the temperature was be- 5 potassium fluoborate. The results show that the mixture tween 450° C. and 600° C.; preferably the pressure of the two salts gave a significantly greater yield of hexa was between 20 and 50 atmospheres. fluorobenzene than either salt alone. CsCls, g. KF, g. KBF4, g. CsIF6, g. CoClFs, g. CsCl2F1, g. CsCl3F3, g. CsClF2, g. CeCls F, g. CoCl6, g. 8.0 12.7 0. 0.66 1.9 2.0 1.0 0.04 O 0. 3.0 0. 7.7 O 0 0 0 0.02 0.24 1. 8.0 12.2 0.25 1.5 1.7 ... 4 0.7 0.04 O () 8.0 12.3 2.5 2.5 1.4 0.4 0.25 0.07 O O (f) in which in was between 4 and 6; the metal fluoride Examples 5 and 6 used was lithium fluoride; and the temperature was be tween 450 C, and 600 C. 20 8.0 g. hexachlorobenzene were heated for 10 hours at In another form of the earlier invention the aromatic 500 C. with sodium fluoride (Example 5) and a mixture compound was a perhalogenobenzene of formula CBrF6 where n is from 1 to 6 inclusive, and the tem- of sodium fluoride with sodium fluoborate (Example 6). perature was between 350° C. and 550° C. The results show a greater extent of fluorination in the In yet another form of the earlier invention the aro- 25 presence of the mixture. No. CoCls, g. NaF, g. NaBF4, g. CF, g. CsClFs, g. CsCl2F, g. CsCl3F, g. CsClF2, g. Co.ClsF, g. C6Cls, g 9---------- 8.0 9.0 O 0. 0. 0.06 0.9 2.5 2.2 0.5 6---------- 8.0 9.0 1.2 0 0.02 0.4 , 8 2.5 ... 5 0.3 matic compound used was a perhalogenonaphthalene of 35 Examples 7 to 12 formula F,e? sois betweeng and 1s and C.8 andErio the tem-in 8.0 g. of hexachlorobenzene were heated withd approxi this case the alkali metal fluoride used was caesium, mately 12 g. of potassium fluoride at 500 for 10 hours. rubidium, potassium or sodium fluoride or mixtures there- The addition to the reaction mixture of the compounds of and the temperature is between 400° C. and 500° C. 40 named in column 4 causes significantly increased extents In another useful sub-division of the process the alkali of fluorination: No.
Recommended publications
  • General Phase Diagram for the KF-Lif-Naf System
    NaF (990˚) General Phase Diagram for the KF-LiF-NaF System after A.G. Bergman and E.P. Dergunov, Compt. rend. acad. sci., U.R.S.S., pp. 31, 754 (1941). 900 800 710˚ 652˚ 700 600 750 500 700 454˚ 800 800 KF 492˚ LiF (856˚) Mol% (844˚) Sodium Fluoride NaF 950˚ KF LiF Potassium Fluoride Lithium Fluoride Sodium Fluoride NaF 940˚ KF LiF Potassium Fluoride Lithium Fluoride Sodium Fluoride NaF 930˚ KF LiF Potassium Fluoride Lithium Fluoride Sodium Fluoride NaF 920˚ KF LiF Potassium Fluoride Lithium Fluoride Sodium Fluoride NaF 910˚ KF LiF Potassium Fluoride Lithium Fluoride Sodium Fluoride NaF 900˚ KF LiF Potassium Fluoride Lithium Fluoride Sodium Fluoride NaF 890˚ KF LiF Potassium Fluoride Lithium Fluoride Sodium Fluoride NaF 880˚ KF LiF Potassium Fluoride Lithium Fluoride Sodium Fluoride NaF 870˚ KF LiF Potassium Fluoride Lithium Fluoride Sodium Fluoride NaF 860˚ KF LiF Potassium Fluoride Lithium Fluoride Sodium Fluoride NaF 850˚ KF LiF Potassium Fluoride Lithium Fluoride Sodium Fluoride NaF 840˚ KF LiF Potassium Fluoride Lithium Fluoride Sodium Fluoride NaF 830˚ KF LiF Potassium Fluoride Lithium Fluoride Sodium Fluoride NaF 820˚ KF LiF Potassium Fluoride Lithium Fluoride Sodium Fluoride NaF 810˚ 810˚ ˚ KF 810 LiF Potassium Fluoride Lithium Fluoride Sodium Fluoride NaF 800˚ 800˚ ˚ KF 800 LiF Potassium Fluoride Lithium Fluoride Sodium Fluoride NaF 790˚ 790˚ ˚ KF 790 LiF Potassium Fluoride Lithium Fluoride Sodium Fluoride NaF 780˚ 780˚ ˚ LiF KF 780 Potassium Fluoride Lithium Fluoride Sodium Fluoride NaF 770˚ 770˚ ˚ LiF KF 770 Potassium Fluoride
    [Show full text]
  • Durham E-Theses
    Durham E-Theses Halogenated diazines and triazines Wood, D. E. How to cite: Wood, D. E. (1978) Halogenated diazines and triazines, Durham theses, Durham University. Available at Durham E-Theses Online: http://etheses.dur.ac.uk/8324/ Use policy The full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that: • a full bibliographic reference is made to the original source • a link is made to the metadata record in Durham E-Theses • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders. Please consult the full Durham E-Theses policy for further details. Academic Support Oce, Durham University, University Oce, Old Elvet, Durham DH1 3HP e-mail: [email protected] Tel: +44 0191 334 6107 http://etheses.dur.ac.uk UNIVERSITY OF Du'RKAM A THESIS entitled HALOGENATED DIAZINES AND TRIAZINES Submitted by D E. WOOD (Grey), B Sc (London) The copyright of this thesis rests with the author No quotation from it should be published without his prior written consent and information derived from it should be acknowledged A candidate for the degree of Doctor of Philosophy 19 78 sr i i > j J To my MoLhcr and FaLhcr WLLII Lh.inks for .ill LhaL Lhey have done ACKNOWLEDGEMLNTS I would like LO express my thanks Lo Professor R D Chambers i under whose guidance this research was undertaken, for considerable encouragement, advice and discussion Thanks are due to Dr R S Matthews for his expert advice with n in r.
    [Show full text]
  • Use of Chlorofluorocarbons in Hydrology : a Guidebook
    USE OF CHLOROFLUOROCARBONS IN HYDROLOGY A Guidebook USE OF CHLOROFLUOROCARBONS IN HYDROLOGY A GUIDEBOOK 2005 Edition The following States are Members of the International Atomic Energy Agency: AFGHANISTAN GREECE PANAMA ALBANIA GUATEMALA PARAGUAY ALGERIA HAITI PERU ANGOLA HOLY SEE PHILIPPINES ARGENTINA HONDURAS POLAND ARMENIA HUNGARY PORTUGAL AUSTRALIA ICELAND QATAR AUSTRIA INDIA REPUBLIC OF MOLDOVA AZERBAIJAN INDONESIA ROMANIA BANGLADESH IRAN, ISLAMIC REPUBLIC OF RUSSIAN FEDERATION BELARUS IRAQ SAUDI ARABIA BELGIUM IRELAND SENEGAL BENIN ISRAEL SERBIA AND MONTENEGRO BOLIVIA ITALY SEYCHELLES BOSNIA AND HERZEGOVINA JAMAICA SIERRA LEONE BOTSWANA JAPAN BRAZIL JORDAN SINGAPORE BULGARIA KAZAKHSTAN SLOVAKIA BURKINA FASO KENYA SLOVENIA CAMEROON KOREA, REPUBLIC OF SOUTH AFRICA CANADA KUWAIT SPAIN CENTRAL AFRICAN KYRGYZSTAN SRI LANKA REPUBLIC LATVIA SUDAN CHAD LEBANON SWEDEN CHILE LIBERIA SWITZERLAND CHINA LIBYAN ARAB JAMAHIRIYA SYRIAN ARAB REPUBLIC COLOMBIA LIECHTENSTEIN TAJIKISTAN COSTA RICA LITHUANIA THAILAND CÔTE D’IVOIRE LUXEMBOURG THE FORMER YUGOSLAV CROATIA MADAGASCAR REPUBLIC OF MACEDONIA CUBA MALAYSIA TUNISIA CYPRUS MALI TURKEY CZECH REPUBLIC MALTA UGANDA DEMOCRATIC REPUBLIC MARSHALL ISLANDS UKRAINE OF THE CONGO MAURITANIA UNITED ARAB EMIRATES DENMARK MAURITIUS UNITED KINGDOM OF DOMINICAN REPUBLIC MEXICO GREAT BRITAIN AND ECUADOR MONACO NORTHERN IRELAND EGYPT MONGOLIA UNITED REPUBLIC EL SALVADOR MOROCCO ERITREA MYANMAR OF TANZANIA ESTONIA NAMIBIA UNITED STATES OF AMERICA ETHIOPIA NETHERLANDS URUGUAY FINLAND NEW ZEALAND UZBEKISTAN FRANCE NICARAGUA VENEZUELA GABON NIGER VIETNAM GEORGIA NIGERIA YEMEN GERMANY NORWAY ZAMBIA GHANA PAKISTAN ZIMBABWE The Agency’s Statute was approved on 23 October 1956 by the Conference on the Statute of the IAEA held at United Nations Headquarters, New York; it entered into force on 29 July 1957. The Headquarters of the Agency are situated in Vienna.
    [Show full text]
  • 1 Abietic Acid R Abrasive Silica for Polishing DR Acenaphthene M (LC
    1 abietic acid R abrasive silica for polishing DR acenaphthene M (LC) acenaphthene quinone R acenaphthylene R acetal (see 1,1-diethoxyethane) acetaldehyde M (FC) acetaldehyde-d (CH3CDO) R acetaldehyde dimethyl acetal CH acetaldoxime R acetamide M (LC) acetamidinium chloride R acetamidoacrylic acid 2- NB acetamidobenzaldehyde p- R acetamidobenzenesulfonyl chloride 4- R acetamidodeoxythioglucopyranose triacetate 2- -2- -1- -β-D- 3,4,6- AB acetamidomethylthiazole 2- -4- PB acetanilide M (LC) acetazolamide R acetdimethylamide see dimethylacetamide, N,N- acethydrazide R acetic acid M (solv) acetic anhydride M (FC) acetmethylamide see methylacetamide, N- acetoacetamide R acetoacetanilide R acetoacetic acid, lithium salt R acetobromoglucose -α-D- NB acetohydroxamic acid R acetoin R acetol (hydroxyacetone) R acetonaphthalide (α)R acetone M (solv) acetone ,A.R. M (solv) acetone-d6 RM acetone cyanohydrin R acetonedicarboxylic acid ,dimethyl ester R acetonedicarboxylic acid -1,3- R acetone dimethyl acetal see dimethoxypropane 2,2- acetonitrile M (solv) acetonitrile-d3 RM acetonylacetone see hexanedione 2,5- acetonylbenzylhydroxycoumarin (3-(α- -4- R acetophenone M (LC) acetophenone oxime R acetophenone trimethylsilyl enol ether see phenyltrimethylsilyl... acetoxyacetone (oxopropyl acetate 2-) R acetoxybenzoic acid 4- DS acetoxynaphthoic acid 6- -2- R 2 acetylacetaldehyde dimethylacetal R acetylacetone (pentanedione -2,4-) M (C) acetylbenzonitrile p- R acetylbiphenyl 4- see phenylacetophenone, p- acetyl bromide M (FC) acetylbromothiophene 2- -5-
    [Show full text]
  • Novel Approaches Towards the Discovery of Tumor-Selective Histone Deacetylase Inhibitors
    Novel Approaches Towards The Discovery of Tumor-Selective Histone Deacetylase Inhibitors A Dissertation Presented to The Academic Faculty By Idris Raji In Partial Fulfilment of the Requirements for the Degree Doctor of Philosophy in Chemistry School of Chemistry and Biochemistry Georgia Institute of Technology, Atlanta GA 30332 December 2016 COPYRIGHT 2016 © IDRIS RAJI Novel Approaches Towards The Discovery of Tumor-Selective Histone Deacetylase Inhibitors Committee members: Dr. Adegboyega K. Oyelere, Advisor Dr. Andreas Bommarius School of Chemistry and Biochemistry School of Chemical and Biomolecular Georgia Institute of Technology Engineering Georgia Institute of Technology Dr. M. G. Finn School of Chemistry and Biochemistry Dr. Ravi Bellamkonda Georgia Institute of Technology Pratt’s school of Engineering Duke University Dr. Stefan France School of Chemistry and Biochemistry Georgia Institute of Technology Date Approved: November 4th, 2016 To my mother, Mrs. Jolade Raji AKNOWLEDGEMENTS I have been very fortunate to have met and interact with people who have positively influenced my life since arriving at Georgia Tech for graduate studies. I will be forever grateful to my advisor, Dr. Adegboyega K. Oyelere, for giving me the opportunity to learn in his lab. I joined his lab with minimal research experience, but he has helped to tremendously enrich my knowledge base and instill a level of confidence in me that was previously nonexistent. I am very grateful for his patience, guidance, availability to discuss research progress and the countless recommendation letters he wrote on my behalf. I am greatly indebted to my thesis committee members Dr. M G Finn, Dr. Stefan France, Dr. Ravi Bellamkonda, and Dr.
    [Show full text]
  • "Fluorine Compounds, Organic," In: Ullmann's Encyclopedia Of
    Article No : a11_349 Fluorine Compounds, Organic GU¨ NTER SIEGEMUND, Hoechst Aktiengesellschaft, Frankfurt, Federal Republic of Germany WERNER SCHWERTFEGER, Hoechst Aktiengesellschaft, Frankfurt, Federal Republic of Germany ANDREW FEIRING, E. I. DuPont de Nemours & Co., Wilmington, Delaware, United States BRUCE SMART, E. I. DuPont de Nemours & Co., Wilmington, Delaware, United States FRED BEHR, Minnesota Mining and Manufacturing Company, St. Paul, Minnesota, United States HERWARD VOGEL, Minnesota Mining and Manufacturing Company, St. Paul, Minnesota, United States BLAINE MCKUSICK, E. I. DuPont de Nemours & Co., Wilmington, Delaware, United States 1. Introduction....................... 444 8. Fluorinated Carboxylic Acids and 2. Production Processes ................ 445 Fluorinated Alkanesulfonic Acids ...... 470 2.1. Substitution of Hydrogen............. 445 8.1. Fluorinated Carboxylic Acids ......... 470 2.2. Halogen – Fluorine Exchange ......... 446 8.1.1. Fluorinated Acetic Acids .............. 470 2.3. Synthesis from Fluorinated Synthons ... 447 8.1.2. Long-Chain Perfluorocarboxylic Acids .... 470 2.4. Addition of Hydrogen Fluoride to 8.1.3. Fluorinated Dicarboxylic Acids ......... 472 Unsaturated Bonds ................. 447 8.1.4. Tetrafluoroethylene – Perfluorovinyl Ether 2.5. Miscellaneous Methods .............. 447 Copolymers with Carboxylic Acid Groups . 472 2.6. Purification and Analysis ............. 447 8.2. Fluorinated Alkanesulfonic Acids ...... 472 3. Fluorinated Alkanes................. 448 8.2.1. Perfluoroalkanesulfonic Acids
    [Show full text]
  • Pacs by Chemical Name (Mg/M3) (Pdf)
    Table 4: Protective Action Criteria (PAC) Rev 25 based on applicable 60-minute AEGLs, ERPGs, or TEELs. Values are presented in mg/m3. August 2009 Table 4 is an alphabetical listing of the chemicals in the PAC data set. It provides Chemical Abstract Service Registry Numbers (CASRNs)1, PAC values, and technical information on the source of the PAC values. Table 4 presents all values for TEEL-0, PAC-1, PAC-2, and PAC-3 in mg/m3. The conversion of ppm to mg/m3 is calculated assuming 25 ºC and 760 mm Hg. The columns presented in Table 4 provide the following information: Heading Definition No. The ordered numbering of the chemicals as they appear in this alphabetical listing. Chemical Name The chemical name given to the PAC Development Team. CASRN The Chemical Abstract Service Registry Number for this chemical. TEEL-0 This is the threshold concentration below which most people will experience no adverse health effects. This PAC is always based on TEEL-0 because AEGL-0 or ERPG-0 values do not exist. PAC-1 Based on the applicable AEGL-1, ERPG-1, or TEEL-1 value. PAC-2 Based on the applicable AEGL-2, ERPG-2, or TEEL-2 value. PAC-3 Based on the applicable AEGL-3, ERPG-3, or TEEL-3 value. Source of PACs: Technical comments provided by the PAC development team that TEEL-0, PAC-1, indicate the source of the data used to derive PAC values. Future efforts PAC-2, PAC-3 are directed at reviewing, revising, and enhancing this information.
    [Show full text]
  • WO 2016/074683 Al 19 May 2016 (19.05.2016) W P O P C T
    (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2016/074683 Al 19 May 2016 (19.05.2016) W P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C12N 15/10 (2006.01) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (21) International Application Number: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, PCT/DK20 15/050343 DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (22) International Filing Date: HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, 11 November 2015 ( 11. 1 1.2015) KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, (25) Filing Language: English PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, (26) Publication Language: English SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: PA 2014 00655 11 November 2014 ( 11. 1 1.2014) DK (84) Designated States (unless otherwise indicated, for every 62/077,933 11 November 2014 ( 11. 11.2014) US kind of regional protection available): ARIPO (BW, GH, 62/202,3 18 7 August 2015 (07.08.2015) US GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, (71) Applicant: LUNDORF PEDERSEN MATERIALS APS TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, [DK/DK]; Nordvej 16 B, Himmelev, DK-4000 Roskilde DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, (DK).
    [Show full text]
  • Gas Conversion Factor for 300 Series
    300GasTable Rec # Gas Symbol GCF Density (g/L) Density (g/L) 25° C / 1 atm 0° C / 1 atm 1 Acetic Acid C2H4F2 0.4155 2.7 2.947 2 Acetic Anhydride C4H6O3 0.258 4.173 4.555 3 Acetone C3H6O 0.3556 2.374 2.591 4 Acetonitryl C2H3N 0.5178 1.678 1.832 5 Acetylene C2H2 0.6255 1.064 1.162 6 Air Air 1.0015 1.185 1.293 7 Allene C3H4 0.4514 1.638 1.787 8 Ammonia NH3 0.7807 0.696 0.76 9 Argon Ar 1.4047 1.633 1.782 10 Arsine AsH3 0.7592 3.186 3.478 11 Benzene C6H6 0.3057 3.193 3.485 12 Boron Trichloride BCl3 0.4421 4.789 5.228 13 Boron Triflouride BF3 0.5431 2.772 3.025 14 Bromine Br2 0.8007 6.532 7.13 15 Bromochlorodifluoromethane CBrClF2 0.3684 6.759 7.378 16 Bromodifluoromethane CHBrF2 0.4644 5.351 5.841 17 Bromotrifluormethane CBrF3 0.3943 6.087 6.644 18 Butane C4H10 0.2622 2.376 2.593 19 Butanol C4H10O 0.2406 3.03 3.307 20 Butene C4H8 0.3056 2.293 2.503 21 Carbon Dioxide CO2 0.7526 1.799 1.964 22 Carbon Disulfide CS2 0.616 3.112 3.397 23 Carbon Monoxide CO 1.0012 1.145 1.25 24 Carbon Tetrachloride CCl4 0.3333 6.287 6.863 25 Carbonyl Sulfide COS 0.668 2.456 2.68 26 Chlorine Cl2 0.8451 2.898 3.163 27 Chlorine Trifluoride ClF3 0.4496 3.779 4.125 28 Chlorobenzene C6H5Cl 0.2614 4.601 5.022 29 Chlorodifluoroethane C2H3ClF2 0.3216 4.108 4.484 30 Chloroform CHCl3 0.4192 4.879 5.326 31 Chloropentafluoroethane C2ClF5 0.2437 6.314 6.892 32 Chloropropane C3H7Cl 0.308 3.21 3.504 33 Cisbutene C4H8 0.3004 2.293 2.503 34 Cyanogen C2N2 0.4924 2.127 2.322 35 Cyanogen Chloride ClCN 0.6486 2.513 2.743 36 Cyclobutane C4H8 0.3562 2.293 2.503 37 Cyclopropane C3H6 0.4562
    [Show full text]
  • Synthesis of Hexafluorobenzene Through Batch Reactive Distillation
    SYNTHESIS OF HEXAFLUOROBENZENE THROUGH BATCH REACTIVE DISTILLATION Jesita Reddy [Bsc. Eng.] In fulfilment of the requirements for the degree Master of Science in Engineering, College of Agriculture, Engineering and Science, University of KwaZulu-Natal December 2018 Supervisors: Doctor David Lokhat and Professor Deresh Ramjugernath As the candidate’s supervisor I agree to the submission of this thesis: Dr. D. Lokhat Prof. D. Ramjugernath DECLARATION I, Jesita Reddy declare that: The research reported in this dissertation/thesis, except where otherwise indicated, is my original work. 1. The research reported in this thesis, except where otherwise indicated, is my original research. 2. This thesis has not been submitted for any degree or examination at any other university. 3. This thesis does not contain other persons’ data, pictures, graphs or other information, unless specifically acknowledged as being sourced from other persons. 4. This thesis does not contain other persons' writing, unless specifically acknowledged as being sourced from other researchers. Where other written sources have been quoted, then: i. Their words have been re-written but the general information attributed to them has been referenced ii. Where their exact words have been used, then their writing has been placed in italics and inside quotation marks, and referenced. 5. This thesis does not contain text, graphics or tables copied and pasted from the Internet, unless specifically acknowledged, and the source being detailed in the thesis and in the References sections. Signed: ________________ Date: ____13/03/19____________ ii ACKNOWLEDGEMENTS This research was affiliated with the Fluorochemical Expansion Initiative recognized by the Department of Science and Technology.
    [Show full text]
  • Reaction of Potassium Fluoride with Organic Halogen Compounds. I
    Reaction of Potassium Fluoride with Organic Halogen Compounds. I) Reactions of Potassium Fluoride with Organic Halides, Acids, aad Esters in presence ef Dimethyl Formamide and their Pyrolytic Decaboxylation in presence of Potassium Fluoride By You Sun Kim Atomic Energy Research Institute, Korea 有機 할로겐 化合物과 弗化加里의 反應 (第1報) 有機 할라어드, 酸 및 에스테르와 弗化加里의 디메칠 호쁨아마이드 溶蝶系 反應 및 高混■■脫炭酸-熱分解反應 金 裕 *善 (1963. 6. 19 受理) Abstract Reactions between potassium fluride with organic halogen-containning carboxylic acids in dimethyl formamide solvent gave a decarboxylation reaction for the case of fluoro carboxylic acids of the type of CF3 COOH, C3F7COOH, and C2F5COOH, whereas an additional partial fluorination together with dimeri­ zation reaction occured for the chlorine containning acids of the type of CH2CICOOH, CH3CHCICOOH, CHCI2COOH and o-Cl-CeHi-COOH. The phenyl halides showed no reactivity, but the halides with two electron attracting substituents on the benzene ring gave mainly dimerization reaction. The esters and alcohols gave an usual fluorination reaction. The same reactions in absence of the solvent at the elevated temperature increase the yield of the dimerized product and gave the cyclized product, fluorenone, in case of o-chlorobenzoic acid. It was found that the fluorination usually precede the decarboxylation reaction by checking the stiochemical sequence of reaction. Catalytic influence of potassium fluoride were discussed and the mechanism of the reaction was considered. 耍 約 「디메望호름아마이드」溶媒系에서 有機含할로겐化合物을 弗化加里와 反應시켜 본 結果 CFsCOOH, CsF’COOH, CzFQOOH 와 같은 含弗素有機酸에서는 脫炭酸反應이 일어나며, 含鹽素有機酸, CH2C1COOH. CH3CHC1COOH, CHC12- COOH 및 o-CK사LCOOH 은 一部 弗化反應이 일어 나고 雙合어imerization) 反應이 隨伴된다는 것을 究明하였다.
    [Show full text]
  • Downloaded for Personal Non-Commercial Research Or Study, Without Prior Permission Or Charge
    https://theses.gla.ac.uk/ Theses Digitisation: https://www.gla.ac.uk/myglasgow/research/enlighten/theses/digitisation/ This is a digitised version of the original print thesis. Copyright and moral rights for this work are retained by the author A copy can be downloaded for personal non-commercial research or study, without prior permission or charge This work cannot be reproduced or quoted extensively from without first obtaining permission in writing from the author The content must not be changed in any way or sold commercially in any format or medium without the formal permission of the author When referring to this work, full bibliographic details including the author, title, awarding institution and date of the thesis must be given Enlighten: Theses https://theses.gla.ac.uk/ [email protected] RADIOTRACER STUDIES OF THE CHLOROFLUORINATION OF SULPHUR TETRAFLUORIDE AT MERCURY(II) FLUORIDE Thesis submitted to the University of Glasgow for the degree of M.Sc BY MOHAMED SELOUGHA FACULTY OF SCIENCE DEPARTMENT OF CHEMISTRY SEPTEMBER 1990 ProQuest Number: 11007548 All rights reserved INFORMATION TO ALL USERS The quality of this reproduction is dependent upon the quality of the copy submitted. In the unlikely event that the author did not send a com plete manuscript and there are missing pages, these will be noted. Also, if material had to be removed, a note will indicate the deletion. uest ProQuest 11007548 Published by ProQuest LLC(2018). Copyright of the Dissertation is held by the Author. All rights reserved. This work is protected against unauthorized copying under Title 17, United States C ode Microform Edition © ProQuest LLC.
    [Show full text]